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Let’s get something straight, shoes are no mere accessories. With pairs typically ranging in price from eighty bucks to several thousand dollars, you could be laying down some serious cash for your kicks. But shoes aren’t just a financial commitment; they’re also an investment in your comfort, confidence, and style. So like any investor who’s got money — or the title of Best Dressed — on the line, it’s time to educate yourself about how you can ensure maximum footwear ROI.

Types of dress shoes:

The words oxford, derby, and brogue are often used interchangeably, but they all refer to specific shoe attributes. Knowing which is which will help you select the perfect style for the occasion and ensure you’re on your way to shoe connoisseurship.

Oxford: A formal style with “closed lacing.” This means the part of the shoe where the eyelets are located is stitched under the vamp, creating a sleek, streamlined appearance. Oxfords will perfectly complement your sharpest suit, and look right at home at upscale events or business affairs.

Derby: A versatile style with “open lacing.” This means the part of the shoe where the eyelets are located is open at the bottom, creating a shoe with a more casual aesthetic. Derbies are a true wardrobe workhorse, easily paired with suits, chinos, or jeans alike.

Brogue: Any shoe (oxfords and derbies included), which features the traditional perforated detailing commonly known as broguing. These may incorporate a cap toe, toe medallion, or wingtip motif.

Construction Techniques:

Dress shoes, like cars, are all built a little differently. It helps to know what your objectives are when shopping, or you may end up with a fickle Fiat when you actually want an Audi. Ask yourself whether you’re looking for a trendy statement shoe to last you through next season, or footwear you can grow old with, because a shoe’s construction can make all the difference.

Goodyear Welting:
How it works: This is the oldest and most labor intensive construction technique, incorporating multiple layers of leather and double-layer stitching to create an outstandingly durable shoe.

Pros: Goodyear shoes are incredibly easy to resole, meaning it’s possible to get years, if not decades, of use from them. Thanks to the additional layers of material, the soles are extremely water-resistant and supportive.

Cons: Greater labor and more materials means they tend to be expensive. Additional layers may also sacrifice some of the shoe’s flexibility.

The Blake Stitch:
How it works: The upper is wrapped around the insole and attached between it and the outsole. A single stitch attaches everything together.

Pros: The Blake is a relatively simple stitching technique. It requires fewer layers of material than the Goodyear, which results in a less expensive, more flexible shoe. It can also be resoled.

Cons: Shoes with this method need a specific Blake machine to be resoled, which means having them repaired could prove difficult. They’re also less water-resistant than their Goodyear constructed counterparts.

Cementing:
How it works: The sole is attached using an adhesive, rather than stitching.

Pros: Because they’re not labor-intensive to make, cemented shoes tend to be very affordable. Cementing is also a more effective technique for the gummy, rubbery soles of casual shoes like sneakers or chukkas.

Cons: Cemented shoes are less durable, and can’t be resoled once they’re worn out.

Tips for saving your soles:

“Worn out” doesn’t mean “throw out.” High quality shoes are built to last, but they’re also built to have their parts replaced as wear accumulates. Have your local cobbler install taps (metal or plastic pieces that prevent the heel or sole from grinding down through use), or ask them to replace your heels and soles as needed.

Branch out with shoe trees. A simple solution that helps prolong the life of any shoes, cedar wood shoe trees will prevent leather from cracking, deteriorating, or becoming misshapen by absorbing the moisture left behind by sweaty feet.

Look polished — literally. Polishing your shoes on the regular will not only keep you looking sharp, but save you money. Polish helps weather-proof your shoes, reduces the damage of scrapes and scuffs, and moisturizes the leather to stop it from cracking. Keep some neutral polish on hand and get in the habit of buffing up your boys every few weeks to keep them at their best.

Tips for building your outfit from the ground up:

Everything other than black is the new black. There’s no law that says formal occasions call exclusively for a black shoe. Take a risk on taupe, cognac, oxblood, or anthracite — each is really just a fancy word for “neutral.”

Up the ante with statement socks. There are few things as charming as the moment a man in a stately suit crosses his legs to reveal a cheeky flash of day-glow paisley at the ankle. Use your socks as a covert way to express yourself, even within the most conservative of dress codes.

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